Electron density studies on hydrogen bonding in two chromone derivatives

The experimental electron densities of two chromone derivatives have been determined from X-ray synchrotron diffraction data at low temperature (100 K). Topological analysis of the electron density has been used to analyze the formation of resonance-assisted hydrogen bonds (RAHBs). Geometrical and topological parameters confirm π-electron delocalization within the hydrogen-bonded ring. In addition, weak C—H...O interactions were identified in both structures. Hydrogen-bond energies allowed medium and weak hydrogen bonds to be distinguished.

Computing details

For both structures, data collection: MarCCD (Paulmann & Morgenroth, 2006); cell refinement: XDS (Kabsch, 1993); data reduction: XDS (Kabsch, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: Volkov et al., (2006); molecular graphics: Volkov et al., (2006); software used to prepare material for publication: Volkov et al., (2006).

3-(Amino-phenyl-methylene)chroman-2,4-dione (I)

Crystal data

C16H11NO3	F(000) = 1104
Mr = 265.26	Dx = 1.376 Mg m^−3
Orthorhombic, Pbca	Synchrotron radiation, λ = 0.6000 Å
Hall symbol: -P 2ac 2ab	θ = 2.6–42.0°
a = 12.925 (3) Å	µ = 0.10 mm^−1
b = 8.273 (2) Å	T = 100 K
c = 23.954 (5) Å	Block, colorless
V = 2561.4 (9) Å^3	0.35 × 0.28 × 0.20 mm
Z = 8

Data collection

Huber diffractometer	Rint = 0.036
Radiation source: synchrotron	θmax = 41.8°, θmin = 1.4°
φ scan	h = −28→27
200890 measured reflections	k = −15→18
14726 independent reflections	l = −53→53
12633 reflections with I > 2σ(I)

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters not defined?
R[F^2 > 2σ(F^2)] = 0.025	w2 = 1/[s^2(Fo^2)]
wR(F^2) = 0.048	(Δ/σ)max < 0.001
S = 2.28	Δρmax = 0.21 e Å^−3
12657 reflections	Δρmin = −0.22 e Å^−3
438 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O(1)	0.727882 (14)	0.26809 (2)	0.146160 (8)	0.018
O(2)	0.682719 (14)	0.25170 (2)	0.234281 (8)	0.018
O(4)	0.456580 (15)	0.06108 (3)	0.091879 (8)	0.021
N(1)	0.411968 (17)	−0.00965 (3)	0.194690 (9)	0.021
C(31)	0.502185 (17)	0.05238 (3)	0.209361 (9)	0.015
C(3)	0.567074 (17)	0.12818 (3)	0.168542 (9)	0.014
C(2)	0.658555 (17)	0.21626 (3)	0.186274 (10)	0.015
C(4)	0.539003 (18)	0.12246 (3)	0.109857 (10)	0.016
C(5)	0.59821 (2)	0.18374 (3)	0.011860 (10)	0.020
C(6)	0.67413 (2)	0.23781 (3)	−0.024966 (11)	0.023
C(7)	0.76793 (2)	0.29983 (3)	−0.004083 (12)	0.024
C(8)	0.78520 (2)	0.30795 (3)	0.053397 (12)	0.021
C(9)	0.707881 (19)	0.25339 (3)	0.089835 (10)	0.016
C(10)	0.614711 (18)	0.18988 (3)	0.069915 (10)	0.016
C(311)	0.530402 (17)	0.02983 (3)	0.269314 (9)	0.014
C(312)	0.620330 (18)	−0.05577 (3)	0.283574 (11)	0.018
C(313)	0.64259 (2)	−0.08679 (4)	0.339651 (12)	0.023
C(314)	0.57630 (3)	−0.03037 (4)	0.381721 (11)	0.025
C(315)	0.48636 (3)	0.05487 (4)	0.367382 (11)	0.025
C(316)	0.46265 (2)	0.08368 (3)	0.311135 (11)	0.019
H(1)	0.388176	−0.002914	0.154639	0.036
H(2)	0.370831	−0.076907	0.222012	0.036
H(5)	0.525138	0.134505	−0.002519	0.040
H(6)	0.662474	0.234209	−0.069722	0.043
H(7)	0.827827	0.339361	−0.032554	0.043
H(8)	0.858139	0.354821	0.068724	0.041
H(312)	0.669382	−0.095902	0.249572	0.033
H(313)	0.709487	−0.15567	0.35293	0.043
H(314)	0.593367	−0.057323	0.424938	0.044
H(315)	0.433167	0.092696	0.399776	0.043
H(316)	0.391666	0.14458	0.299402	0.038

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01407 (6)	0.02108 (8)	0.01839 (7)	−0.00469 (6)	0.00008 (5)	−0.00065 (6)
O(2)	0.01600 (7)	0.02155 (8)	0.01669 (7)	−0.00326 (6)	−0.00265 (5)	−0.00420 (6)
O(4)	0.01812 (8)	0.02913 (10)	0.01558 (7)	−0.00853 (7)	−0.00412 (6)	0.00065 (6)
N(1)	0.01511 (8)	0.03061 (12)	0.01775 (8)	−0.00822 (8)	−0.00302 (6)	0.00447 (7)
C(31)	0.01167 (7)	0.01841 (9)	0.01437 (7)	−0.00164 (6)	−0.00094 (6)	0.00012 (6)
C(3)	0.01205 (7)	0.01687 (8)	0.01384 (7)	−0.00220 (6)	−0.00098 (6)	−0.00089 (6)
C(2)	0.01201 (7)	0.01630 (8)	0.01574 (8)	−0.00174 (6)	−0.00129 (6)	−0.00234 (6)
C(4)	0.01445 (8)	0.01834 (9)	0.01389 (7)	−0.00306 (7)	−0.00153 (6)	−0.00041 (6)
C(5)	0.02344 (11)	0.02064 (10)	0.01497 (8)	−0.00152 (9)	0.00040 (8)	0.00121 (7)
C(6)	0.02972 (14)	0.02215 (11)	0.01709 (9)	−0.00061 (10)	0.00451 (9)	0.00295 (8)
C(7)	0.02673 (13)	0.02198 (11)	0.02226 (11)	−0.00195 (10)	0.00772 (9)	0.00365 (9)
C(8)	0.01956 (10)	0.02031 (10)	0.02312 (11)	−0.00355 (8)	0.00495 (8)	0.00220 (8)
C(9)	0.01533 (8)	0.01591 (8)	0.01783 (9)	−0.00189 (7)	0.00202 (7)	0.00039 (7)
C(10)	0.01645 (8)	0.01622 (8)	0.01472 (8)	−0.00136 (7)	0.00031 (6)	0.00011 (6)
C(311)	0.01245 (7)	0.01697 (8)	0.01382 (7)	0.00092 (6)	−0.00008 (6)	−0.00082 (6)
C(312)	0.01343 (8)	0.02095 (10)	0.01910 (9)	0.00214 (7)	−0.00130 (7)	0.00054 (7)
C(313)	0.01997 (10)	0.02553 (12)	0.02311 (11)	−0.00185 (9)	−0.00747 (9)	0.00539 (9)
C(314)	0.03451 (15)	0.02584 (12)	0.01590 (9)	−0.00693 (11)	−0.00545 (10)	0.00150 (8)
C(315)	0.03463 (15)	0.02345 (12)	0.01570 (9)	−0.00055 (11)	0.00522 (9)	−0.00286 (8)
C(316)	0.01958 (10)	0.02002 (10)	0.01775 (9)	0.00356 (8)	0.00421 (7)	−0.00094 (7)
H(1)	0.029884	0.053306	0.025589	−0.011947	−0.007611	0.005823
H(2)	0.028722	0.048954	0.030494	−0.014086	0.000806	0.00805
H(5)	0.040022	0.051368	0.02884	−0.015758	−0.006526	0.000876
H(6)	0.058798	0.048425	0.021737	−0.007992	0.00402	0.00114
H(7)	0.042092	0.048918	0.03737	−0.006625	0.01722	0.006043
H(8)	0.027153	0.053085	0.042921	−0.012951	0.002344	0.003671
H(312)	0.029651	0.04065	0.027709	0.008638	0.0038	0.000443
H(313)	0.035942	0.055535	0.036084	0.01124	−0.007949	0.010651
H(314)	0.054974	0.055115	0.02103	−0.000162	−0.005984	0.004664
H(315)	0.051921	0.04915	0.027389	0.007242	0.013236	−0.002218
H(316)	0.030317	0.047784	0.034859	0.01279	0.004744	0.003995

Geometric parameters (Å, º)

O(1)—C(2)	1.3821 (3)	C(7)—C(8)	1.3965 (4)
O(1)—C(9)	1.3791 (3)	C(7)—H(7)	1.0823
O(2)—C(2)	1.2272 (3)	C(8)—C(9)	1.4015 (3)
O(4)—C(4)	1.2562 (3)	C(8)—H(8)	1.0835
N(1)—C(31)	1.3216 (3)	C(9)—C(10)	1.3978 (3)
N(1)—H(1)	1.0090	C(311)—C(312)	1.4033 (3)
N(1)—H(2)	1.0102	C(311)—C(316)	1.4032 (3)
C(31)—C(3)	1.4327 (3)	C(312)—C(313)	1.3975 (4)
C(31)—C(311)	1.4934 (3)	C(312)—H(312)	1.0842
C(3)—C(2)	1.4524 (3)	C(313)—C(314)	1.4026 (4)
C(3)—C(4)	1.4526 (3)	C(313)—H(313)	1.0833
C(4)—C(10)	1.4778 (3)	C(314)—C(315)	1.4023 (5)
C(5)—C(6)	1.3932 (4)	C(314)—H(314)	1.0817
C(5)—C(10)	1.4078 (3)	C(315)—C(316)	1.4022 (4)
C(5)—H(5)	1.0847	C(315)—H(315)	1.0830
C(6)—C(7)	1.4084 (4)	C(316)—H(316)	1.0838
C(6)—H(6)	1.0830
C(2)—O(1)—C(9)	122.09 (2)	C(7)—C(8)—H(8)	119.36
C(31)—N(1)—H(1)	120.02	C(9)—C(8)—H(8)	121.64
C(31)—N(1)—H(2)	120.40	O(1)—C(9)—C(8)	116.57 (2)
H(1)—N(1)—H(2)	119.08	O(1)—C(9)—C(10)	121.91 (2)
N(1)—C(31)—C(3)	120.33 (2)	C(8)—C(9)—C(10)	121.52 (2)
N(1)—C(31)—C(311)	115.00 (2)	C(4)—C(10)—C(5)	121.71 (2)
C(3)—C(31)—C(311)	124.61 (2)	C(4)—C(10)—C(9)	119.43 (2)
C(31)—C(3)—C(2)	119.77 (2)	C(5)—C(10)—C(9)	118.77 (2)
C(31)—C(3)—C(4)	120.00 (2)	C(31)—C(311)—C(312)	119.96 (2)
C(2)—C(3)—C(4)	120.18 (2)	C(31)—C(311)—C(316)	119.63 (2)
O(1)—C(2)—O(2)	114.35 (2)	C(312)—C(311)—C(316)	120.22 (2)
O(1)—C(2)—C(3)	118.70 (2)	C(311)—C(312)—C(313)	119.81 (2)
O(2)—C(2)—C(3)	126.95 (2)	C(311)—C(312)—H(312)	117.13
O(4)—C(4)—C(3)	123.83 (2)	C(313)—C(312)—H(312)	123.06
O(4)—C(4)—C(10)	119.48 (2)	C(312)—C(313)—C(314)	120.25 (3)
C(3)—C(4)—C(10)	116.67 (2)	C(312)—C(313)—H(313)	122.90
C(6)—C(5)—C(10)	120.47 (3)	C(314)—C(313)—H(313)	116.85
C(6)—C(5)—H(5)	122.19	C(313)—C(314)—C(315)	119.85 (2)
C(10)—C(5)—H(5)	117.33	C(313)—C(314)—H(314)	119.63
C(5)—C(6)—C(7)	119.89 (3)	C(315)—C(314)—H(314)	120.47
C(5)—C(6)—H(6)	121.33	C(314)—C(315)—C(316)	120.14 (2)
C(7)—C(6)—H(6)	118.77	C(314)—C(315)—H(315)	119.74
C(6)—C(7)—C(8)	120.35 (2)	C(316)—C(315)—H(315)	120.04
C(6)—C(7)—H(7)	120.14	C(311)—C(316)—C(315)	119.71 (2)
C(8)—C(7)—H(7)	119.50	C(311)—C(316)—H(316)	119.39
C(7)—C(8)—C(9)	118.99 (3)	C(315)—C(316)—H(316)	120.88

3-(Methylamino-phenyl-methylene)chroman-2,4-dione (II)

Crystal data

C17H13NO3	Z = 4
Mr = 279.28	F(000) = 584
Monoclinic, P21/c	Dx = 1.369 Mg m^−3
Hall symbol: -P 2ybc	Synchrotron radiation, λ = 0.6000 Å
a = 9.292 (2) Å	θ = 2.0–45.0°
b = 14.145 (2) Å	µ = 0.10 mm^−1
c = 11.012 (2) Å	T = 100 K
β = 110.576 (3)°	Ball, colorless
V = 1355.0 (4) Å^3	0.55 × 0.5 × 0.45 mm

Data collection

Huber diffractometer	Rint = 0.023
Radiation source: synchrotron	θmax = 45.0°, θmin = 2.0°
φ scan	h = −21→20
117495 measured reflections	k = −33→31
17962 independent reflections	l = −25→24
16260 reflections with I > 2σ(I)

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters not defined?
R[F^2 > 2σ(F^2)] = 0.025	w2 = 1/[s^2(Fo^2)]
wR(F^2) = 0.053	(Δ/σ)max < 0.001
S = 2.99	Δρmax = 0.22 e Å^−3
16349 reflections	Δρmin = −0.23 e Å^−3
464 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O(1)	0.37210 (2)	0.174184 (14)	0.17365 (2)	0.022
O(2)	0.20609 (3)	0.234141 (15)	−0.00522 (3)	0.025
O(4)	0.36848 (2)	−0.085913 (12)	0.006925 (18)	0.018
N(1)	0.14117 (2)	−0.030363 (13)	−0.195456 (19)	0.019
C(2)	0.27325 (2)	0.162800 (12)	0.046176 (19)	0.018
C(3)	0.26115 (2)	0.068683 (11)	−0.011357 (17)	0.016
C(4)	0.364542 (19)	−0.006173 (11)	0.056018 (16)	0.015
C(5)	0.56027 (2)	−0.057892 (12)	0.268345 (17)	0.018
C(6)	0.64641 (2)	−0.040092 (14)	0.397772 (18)	0.021
C(7)	0.63845 (3)	0.049442 (15)	0.450607 (19)	0.023
C(8)	0.54642 (3)	0.120815 (14)	0.374644 (19)	0.023
C(9)	0.45992 (2)	0.101431 (12)	0.244773 (18)	0.018
C(10)	0.464392 (18)	0.012670 (10)	0.190718 (15)	0.016
C(31)	0.14607 (2)	0.051532 (11)	−0.135568 (16)	0.015
C(33)	0.02359 (3)	−0.060533 (14)	−0.31689 (2)	0.025
C(311)	0.02005 (2)	0.119985 (10)	−0.199755 (15)	0.015
C(312)	−0.10243 (2)	0.125929 (11)	−0.154223 (16)	0.017
C(313)	−0.22782 (2)	0.184425 (11)	−0.216521 (18)	0.019
C(314)	−0.23188 (3)	0.236043 (12)	−0.325489 (19)	0.021
C(315)	−0.10881 (3)	0.230322 (12)	−0.370848 (18)	0.023
C(316)	0.01772 (2)	0.172442 (12)	−0.308254 (17)	0.020
H(33A)	0.056809	−0.128275	−0.338312	0.050	0.5
H(33B)	0.014328	−0.013554	−0.394305	0.045	0.5
H(33C)	−0.083046	−0.063712	−0.302133	0.043	0.5
H(33D)	−0.06349	−0.008117	−0.345929	0.041	0.5
H(33E)	−0.028085	−0.127278	−0.316953	0.048	0.5
H(33F)	0.086847	−0.083664	−0.374715	0.049	0.5
H(1)	0.225783	−0.073097	−0.14019	0.034
H(5)	0.564505	−0.126825	0.227096	0.034
H(6)	0.712798	−0.095708	0.46006	0.037
H(7)	0.705002	0.06473	0.551064	0.042
H(8)	0.538799	0.191417	0.409718	0.044
H(312)	−0.099079	0.083524	−0.071401	0.035
H(313)	−0.32424	0.187114	−0.182951	0.040
H(314)	−0.329475	0.279899	−0.377881	0.039
H(315)	−0.107109	0.271252	−0.453423	0.040
H(316)	0.112675	0.165215	−0.343003	0.037

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.02743 (7)	0.01511 (5)	0.01800 (6)	−0.00054 (5)	0.00162 (6)	−0.00251 (4)
O(2)	0.03015 (8)	0.01462 (6)	0.02396 (8)	0.00189 (5)	0.00057 (7)	−0.00075 (5)
O(4)	0.01850 (5)	0.01644 (5)	0.01641 (5)	0.00202 (4)	0.00238 (5)	−0.00281 (4)
N(1)	0.01919 (6)	0.01685 (5)	0.01636 (6)	0.00211 (5)	0.00091 (5)	−0.00237 (4)
C(2)	0.02071 (6)	0.01365 (5)	0.01794 (6)	−0.00075 (4)	0.00368 (5)	−0.00100 (4)
C(3)	0.01591 (5)	0.01412 (4)	0.01517 (5)	−0.00048 (4)	0.00362 (5)	−0.00092 (4)
C(4)	0.01466 (5)	0.01502 (4)	0.01454 (5)	−0.00046 (4)	0.00348 (4)	−0.00146 (4)
C(5)	0.01639 (5)	0.01840 (5)	0.01643 (5)	−0.00028 (4)	0.00241 (5)	−0.00103 (4)
C(6)	0.02010 (6)	0.02113 (6)	0.01666 (6)	−0.00107 (5)	0.00127 (5)	−0.00030 (5)
C(7)	0.02683 (8)	0.02183 (6)	0.01599 (6)	−0.00246 (5)	0.00065 (6)	−0.00192 (5)
C(8)	0.02891 (8)	0.01874 (6)	0.01652 (6)	−0.00250 (5)	0.00156 (6)	−0.00331 (5)
C(9)	0.02066 (6)	0.01586 (5)	0.01549 (5)	−0.00244 (4)	0.00317 (5)	−0.00187 (4)
C(10)	0.01556 (5)	0.01608 (4)	0.01465 (5)	−0.00150 (4)	0.00320 (4)	−0.00139 (3)
C(31)	0.01546 (5)	0.01475 (5)	0.01473 (5)	0.00000 (4)	0.00394 (5)	0.00004 (4)
C(33)	0.02822 (8)	0.02067 (6)	0.01864 (6)	0.00139 (5)	−0.00234 (6)	−0.00270 (5)
C(311)	0.01715 (5)	0.01468 (4)	0.01405 (4)	0.00052 (4)	0.00499 (4)	0.00204 (4)
C(312)	0.01709 (5)	0.01704 (5)	0.01624 (5)	0.00130 (4)	0.00557 (4)	0.00293 (4)
C(313)	0.01708 (6)	0.01673 (5)	0.02064 (6)	0.00139 (4)	0.00376 (5)	0.00060 (4)
C(314)	0.02323 (7)	0.01512 (5)	0.01890 (6)	0.00195 (5)	0.00008 (6)	0.00167 (5)
C(315)	0.03179 (9)	0.01779 (5)	0.01642 (6)	0.00178 (5)	0.00566 (6)	0.00508 (4)
C(316)	0.02641 (7)	0.01853 (5)	0.01725 (5)	0.00088 (5)	0.00957 (6)	0.00404 (4)
H(33A)	0.067268	0.031507	0.043715	0.016158	0.011263	−0.00817
H(33B)	0.06284	0.039739	0.030299	0.012479	0.014581	0.004668
H(33C)	0.036102	0.037057	0.052853	−0.002855	0.011541	−0.008575
H(33D)	0.043042	0.036695	0.034723	0.016512	0.001158	−0.001466
H(33E)	0.055778	0.026212	0.054849	−0.003338	0.010621	−0.008498
H(33F)	0.059423	0.046181	0.043957	0.011043	0.020863	−0.011779
H(1)	0.033841	0.029335	0.028412	0.009461	−0.000351	−0.002978
H(5)	0.036763	0.025394	0.032507	0.003136	0.003931	−0.00555
H(7)	0.04767	0.041191	0.02396	0.001397	−0.004191	−0.006573
H(8)	0.05613	0.028922	0.034692	0.004613	0.000418	−0.010718
H(313)	0.031923	0.048646	0.041228	0.011917	0.016832	0.009559
H(314)	0.03688	0.034323	0.038888	0.012469	0.005759	0.010575
H(315)	0.044983	0.039033	0.032533	0.001536	0.011058	0.016157
H(316)	0.034455	0.04681	0.033275	0.003489	0.016709	0.009092

Geometric parameters (Å, º)

O(1)—C(2)	1.3906 (3)	C(9)—C(10)	1.3963 (2)
O(1)—C(9)	1.3744 (3)	C(31)—C(311)	1.4922 (2)
O(2)—C(2)	1.2165 (3)	C(33)—H(33A)	1.0584
O(4)—C(4)	1.2569 (2)	C(33)—H(33B)	1.0603
N(1)—C(31)	1.3258 (2)	C(33)—H(33C)	1.0599
N(1)—C(33)	1.4618 (3)	C(33)—H(33D)	1.0606
N(1)—H(1)	1.008	C(33)—H(33E)	1.0591
C(2)—C(3)	1.4616 (2)	C(33)—H(33F)	1.0588
C(3)—C(4)	1.4469 (2)	C(311)—C(312)	1.3982 (2)
C(3)—C(31)	1.4301 (2)	C(311)—C(316)	1.4001 (2)
C(4)—C(10)	1.4713 (2)	C(312)—C(313)	1.3968 (2)
C(5)—C(6)	1.3905 (3)	C(312)—H(312)	1.0829
C(5)—C(10)	1.4090 (2)	C(313)—C(314)	1.3938 (3)
C(5)—H(5)	1.0822	C(313)—H(313)	1.0834
C(6)—C(7)	1.4065 (3)	C(314)—C(315)	1.4018 (3)
C(6)—H(6)	1.082	C(314)—H(314)	1.0828
C(7)—C(8)	1.3955 (3)	C(315)—C(316)	1.3993 (3)
C(7)—H(7)	1.082	C(315)—H(315)	1.0828
C(8)—C(9)	1.3995 (3)	C(316)—H(316)	1.0829
C(8)—H(8)	1.0820
C(2)—O(1)—C(9)	122.53 (2)	N(1)—C(33)—H(33D)	108.50
C(31)—N(1)—C(33)	126.45 (2)	N(1)—C(33)—H(33E)	116.98
C(31)—N(1)—H(1)	109.89	N(1)—C(33)—H(33F)	104.24
C(33)—N(1)—H(1)	123.39	H(33A)—C(33)—H(33B)	109.62
O(1)—C(2)—O(2)	114.99 (2)	H(33A)—C(33)—H(33C)	110.94
O(1)—C(2)—C(3)	117.77 (2)	H(33A)—C(33)—H(33D)	144.79
O(2)—C(2)—C(3)	127.24 (2)	H(33A)—C(33)—H(33E)	50.245
C(2)—C(3)—C(4)	120.55 (2)	H(33A)—C(33)—H(33F)	47.09
C(2)—C(3)—C(31)	119.13 (2)	H(33B)—C(33)—H(33C)	109.50
C(4)—C(3)—C(31)	120.32 (2)	H(33B)—C(33)—H(33D)	58.78
O(4)—C(4)—C(3)	123.41 (2)	H(33B)—C(33)—H(33E)	130.50
O(4)—C(4)—C(10)	119.53 (2)	H(33B)—C(33)—H(33F)	67.38
C(3)—C(4)—C(10)	117.01 (2)	H(33C)—C(33)—H(33D)	54.59
C(6)—C(5)—C(10)	120.47 (2)	H(33C)—C(33)—H(33E)	60.93
C(6)—C(5)—H(5)	120.04	H(33C)—C(33)—H(33F)	145.64
C(10)—C(5)—H(5)	119.47	H(33D)—C(33)—H(33E)	108.98
C(5)—C(6)—C(7)	119.47 (2)	H(33D)—C(33)—H(33F)	124.10
C(5)—C(6)—H(6)	120.81	H(33E)—C(33)—H(33F)	94.10
C(7)—C(6)—H(6)	119.55	C(31)—C(311)—C(312)	118.12 (2)
C(6)—C(7)—C(8)	120.91 (4)	C(31)—C(311)—C(316)	121.49 (2)
C(6)—C(7)—H(7)	120.55	C(312)—C(311)—C(316)	120.25 (1)
C(8)—C(7)—H(7)	118.53	C(311)—C(312)—C(313)	120.21 (2)
C(7)—C(8)—C(9)	118.79 (2)	C(311)—C(312)—H(312)	118.85
C(7)—C(8)—H(8)	123.84	C(313)—C(312)—H(312)	120.92
C(9)—C(8)—H(8)	117.35	C(312)—C(313)—C(314)	119.92 (2)
O(1)—C(9)—C(8)	116.64 (1)	C(312)—C(313)—H(313)	120.02
O(1)—C(9)—C(10)	122.07 (1)	C(314)—C(313)—H(313)	120.00
C(8)—C(9)—C(10)	121.29 (1)	C(313)—C(314)—C(315)	119.86 (2)
C(4)—C(10)—C(5)	121.57 (2)	C(313)—C(314)—H(314)	121.54
C(4)—C(10)—C(9)	119.34 (2)	C(315)—C(314)—H(314)	118.59
C(5)—C(10)—C(9)	119.04 (2)	C(314)—C(315)—C(316)	120.51 (2)
N(1)—C(31)—C(3)	120.49 (2)	C(314)—C(315)—H(315)	121.53
N(1)—C(31)—C(311)	116.57 (2)	C(316)—C(315)—H(315)	117.95
C(3)—C(31)—C(311)	122.79 (1)	C(311)—C(316)—C(315)	119.26 (2)
N(1)—C(33)—H(33A)	106.58	C(311)—C(316)—H(316)	118.77
N(1)—C(33)—H(33B)	112.08	C(315)—C(316)—H(316)	121.94
N(1)—C(33)—H(33C)	108.09